Pyrimidines

Synthetic Route of 330786-24-8, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 330786-24-8 as follows.

To 200L reaction kettle adding 124.60 kg tetrahydrofuran, are added under stirring 3 – (4 -)-1H-[34-D]-4-(SM1)(4.00kg1eq)(S)-1-Oxycarbonyl -3 – hydroxy piperidine (SM2) (7.96 kg, 3eq), triphenylphosphine (10.40 kg, 3eq). 25[…] (will be 8.00 kg, 3eq azo-phthalic acid diisopropyl ester soluble in 8.00 kg of in tetrahydrofuran),325(TLCMonitoring: ethyl acetate: methanol=10:1). Stirring under reduced pressure distillation. Temperature control 15 C, dropwise 24.00kg325The reaction is complete (TLC monitoring: dichloromethane: ethyl acetate=5:3). Dichloromethane is used for extraction of the aqueous phase(60.00kg)45.00kgStirring 30 minutes later, the static layering, the minute eliminates upper organic phase. The remaining aqueous phase is added to the 200L anti-1535.00kg 20(9.60Kg sodium hydroxide into 38.40 kg of pure water), the use of pH test paper monitoring reaction solution, pH=5 – 6(2)100LAdding 19.20v ethanol, 0.10 kg of activated carbon, heated to 75 C reflux stirring 2 hours. 1.60kg100LStop heating, water bath cooling, stirring crystallization, when the temperature is reduced to 25 C, thermal crystallization 2 hours. 5.60kg6012Powder 3.75 kg, yield: 85%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,330786-24-8, its application will become more common.

Reference:
Patent; Beijing Rui Chong Kang Tai Pharmaceutical Research Institute Limited; Gu, Huijuan; Chen, Yan; Zhang, Fan; Li, Wei; Liu, Xiangwei; (18 pag.)CN106146512; (2016); A;,
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Application of 69034-12-4 ,Some common heterocyclic compound, 69034-12-4, molecular formula is C5H2ClF3N2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

1,1-dimethylethyl(1R,4S,6R)-4-(aminomethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate D29 (45 mg) was dissolved in DMSO (1 ml) then DIPEA (0.038 ml, 0.219 mmol) and 2-chloro-5-(trifluoromethyl)pyrimidine (36.3 mg, 0.199 mmol) were added and the mixture was stirred at 100 C. for 4 hours. NaHCO3 saturated solution (10 ml) was added and the aqueous layer was extracted with DCM. The combined organic layers were dried over Na2SO4 anhydrous, filtered through a phase separator tube and concentrated under vacuum to give a crude product which was purified by silica gel chromatography (Biotage SP-column size 25 g, using Cy_EtOAc=9:1 to 5:5 as eluent). It was recovered the title compound D32 (45 mg). UPLC: (Acid Final_QC): rt=0.87, peak observed: 373 (M+1). C17H23F3N4O2 requires 372. 1H NMR (400 MHz, CDCl3) delta ppm 8.68-8.28 (m, 2H) 6.23-5.53 (m, 1H) 4.44-3.32 (m, 5H) 1.97-1.73 (m, 2H) 1.52-1.34 (m, 9H) 1.06-0.94 (m, 2H) 0.80-0.64 (m, 1H) 0.27-0.00 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69034-12-4, its application will become more common.

Reference:
Patent; ALVARO, Giuseppe; Amantini, David; Castiglioni, Emiliano; Di Fabio, Romano; Pavone, Francesca; US2010/144760; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2915-16-4, 2-Chloro-4,6-diphenylpyrimidine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 2915-16-4, blongs to pyrimidines compound. name: 2-Chloro-4,6-diphenylpyrimidine

A mixture of 2-chloro-4,6-diphenylpryimidine, 0. 79G (2.96 mmol), 4- (HYDROXYLMETHYL) phenylboronic acid, 0.45g (2.96 mmol), Pd (PPh3) 4,342mg (0.296 mmol), in 2 mL of toluene and 1ML of methanol was heated to obtain a clear solution. To the solution was added 2mL of 4. OM aq. NA2CO3. The reaction mixture refluxed for 16h at 70 C. The mixture was cooled to room temperature and diluted with LOOML ethyl acetate. The organic layer was washed with water, sat. aq. NaCl, and dried (MGSO4). After the solution was concentrated, the residue was recrystallized with Et20-Heptane (1 : 1) to afford the desired product in 0.38g (38%) as a yellow SOLID. 1H NMR (DMSO-d6) 8.72 (d, 2H, J = 9. 0HZ), 8.52-8. 47 (m, 4H), 8.45 (s, 1H), 7.64-7. 57 (m, 8H), 4.78 (d, 2H, J = 6.7Hz), 4.37 (t, 1H, J = 6.7Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2915-16-4, its application will become more common.

Reference:
Patent; THE INSTITUTES FOR PHARMACEUTICAL DISCOVERY, LLC; WO2004/99171; (2004); A2;,
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Application of 914612-23-0, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 914612-23-0 as follows.

Alternative synthesis for (S)-3-(6-Benzyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester To a solution of (S)-3-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester (6.21 g, 33.16 mmol) and 6-benzyl-4-chloro-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidine (9 g, 34.65 mmol) in 2-Me-THF (100 mL) was added under nitrogen tBuOK (8.17 g, 72.95 mmol). The mixture was stirred at rt for 25 min. The mixture was quenched with H2O. The organic layer was washed with brine. The resulting organic solution was concentrated in vacuo to provide (S)-3-(6-benzyl-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (12.6 g, 89% yield) as a yellow gum.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,914612-23-0, its application will become more common.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo Antonio; FURET, Pascal; HEBACH, Christina; HOGENAUER, Klemens; HOLLINGWORTH, Gregory; KALIS, Christoph; LEWIS, Ian; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STAUFFER, Frederic; STRANG, Ross; STOWASSER, Frank; TUFFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; US2015/342951; (2015); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 1197953-49-3, name is (2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide. A new synthetic method of this compound is introduced below., Computed Properties of C12H12Cl2N3OP

Add compound 8a to a 25 mL single-mouth bottle with magnetic stirrer and condenser(760 mg, 3.21 mmol), compound 5a (1.01 g, 3.21 mmol)And ethylene glycol monomethyl ether (10mL), stir and dissolve, add hydrogen chloride isopropanol solution(4.82mmol, 0.96mL, 5M),The temperature was raised to 120 C under a nitrogen atmosphere and stirred to react overnight. Cool to room temperature,Add water (10 mL) and saturated sodium bicarbonate (5 mL) and dichloromethane (15 mL×3)The organic phase was combined, washed with saturated brine and dried over anhydrous sodium sulfate.Filtration, concentration, and residue over silica gel to give a white solid600 mg, the yield was 36.1%.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 1197953-49-3, (2-((2,5-Dichloropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide.

Reference:
Patent; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Li Huanyin; (49 pag.)CN109851638; (2019); A;,
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Related Products of 108-53-2, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.108-53-2, name is 2-Aminopyrimidin-4(1H)-one, molecular formula is C4H5N3O, molecular weight is 111.102, as common compound, the synthetic route is as follows.

In a three neck IL round bottom flask equipped with reflux condenser was added 2-amino- 4(3H)-pyrimidinone A.ll (10Og, 0.9 mol) (available from Toronto Research Chemicals) followed by POCl3 (168 ml, 1.800mol) at room temperature and under an atmosphere of N2. To this was cautiously added ClSO3H (4.8ml, 72.01 mmol). The solution was heated to 950C for 4 hrs, before it was cooled to room temperature. The solution was then cooled in an ice bath before it was poured into 700ml of ice water with vigorous stirring. Adjusted the pH to ~7 with NH4OH (30% by weight) (temperature was held below 2O0C). A tan colored solid was collected by filtration. The solid was dried under vacuum at 7O0C overnight to afford 4-chloro- 2-pyrimidinamine A.12 (108g, 92%) as an off white solid.1H NMR (400 MHz, (CD)3SO) delta 8.17 (d, J = 5.2 Hz, IH), 7.07 (br s, 2H), 6.64 (d, J = 5.2 Hz, IH); ESI MS: M + H+ 130.0 m/z.

Statistics shows that 108-53-2 is playing an increasingly important role. we look forward to future research findings about 2-Aminopyrimidin-4(1H)-one.

Reference:
Patent; AMGEN INC.; WO2009/158011; (2009); A1;,
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Pyrimidine – Wikipedia

Electric Literature of 16019-33-3 , The common heterocyclic compound, 16019-33-3, name is 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde, molecular formula is C6H4Cl2N2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

(1R,2S,3R,5R)-3-Amino-5-(hydroxymethyl)cyclopentane-1,2-diol hydrochloride (40 g, 218 mmol) was dissolved at room temperature in methanol (400 mL) and 2,2-dimethoxypropane (54 mL, 436 mmol), and methanesulfonic acid(14 mL, 218 mmol) was added thereto dropwise in an ice bath with stirring so as to keep the internal temperature at 7C or lower. After the mixture was stirred in an ice bath for 5 minutes and at room temperature overnight, triethylamine (122 mL, 872 mmol) was added thereto dropwise in an ice bath so as to keep the internal temperature at 10C or lower. After the mixture was stirred in an ice bath for 5 minutes and at room temperature for 30 minutes, the solvent was distilled off under reduced pressure, thereby obtaining the title compound as a crude isomeric mixture (102 g). LCMS (ESI) m/z 188 [M+H]+ The crude isomeric mixture (102 g) of ((3aR,4R,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanol and (4aR,6R,7S,7aR)-6-amino-2,2-dimethylhexahydrocyclopenta[d][1,3]dioxin-7-ol obtained in step 1 of Reference Example 93, and 2-(4,6-dichloropyrimidin-5-yl)acetaldehyde (46 g, 240 mmol) was suspended in 2-butanol (400 mL). Then, triethylamine (61 mL, 436 mmol) was added thereto at room temperature, and the reaction solution was stirred at 80C overnight. After the reaction solvent was distilled off under reduced pressure, the residue was partitioned with the addition of ethyl acetate and an aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline, and dried over sodium sulfate, followed by distilling off the solvent, thereby obtaining the title compound as a crude isomeric mixture (72 g). LCMS (ESI) m/z 324 [M+H]+

The synthetic route of 16019-33-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Taiho Pharmaceutical Co., Ltd.; ISHIDA, Keiji; (139 pag.)EP3395345; (2018); A1;,
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Reference of 5750-76-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 5750-76-5, name is 2,4,5-Trichloropyrimidine, molecular formula is C4HCl3N2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A mixture of 2- (isopropylsulfonyl) aniline (1 g, 5 mmol)And 2,4,5-trichloropyrimidine (1.1 g, 6 mmol)Was dissolved in N, N-dimethylformamide (30 mL)Sodium hydride (60%, 0.4 g, 10 mmol) was added,25 C for 12 hours.(30 mL x 3), the organic phase was combined, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated in vacuo,The crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 25: 1)The product (0.8 g, yield 46%) was obtained.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 5750-76-5, 2,4,5-Trichloropyrimidine.

Reference:
Patent; Shandong Xuanzhu Pharma Co., Ltd.; Wu, Yongqian; (21 pag.)CN106146525; (2016); A;,
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Electric Literature of 131860-97-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 131860-97-4, name is (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate, molecular formula is C15H13ClN2O4, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Methyl (£)-2-{2-[6-chloropyiimidin-4-yloxy]phenyl}-3-methoxyacrylate (E) (3g of 95.4% strength) was charged to the reaction tube followed by the solvent (10 ml) then 2- cyanophenol (1.2g), base (1.5 mol equivalents) and the compound being tested as a catalyst (15 mol%). The reaction mixtures were held, with stirring, at 400C for 4hrs, then at 6O0C for 2 hrs. The reaction was monitored for formation of product, throughout the hold period, by Gas Chromatography. Results are recorded as area % levels of methyl (£)-2-{2-[6- chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (II) and methyl (E)-2-{2-[6-(2- cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (I) in the reaction mixture.The following systems were tested:TABLE l The results are shown in Table 2 below:TABLE 2

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 131860-97-4, (E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate.

Reference:
Patent; SYNGENTA LIMITED; WO2008/43977; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 769-42-6, 1,3-Dimethylbarbituric acid, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, category: pyrimidines, blongs to pyrimidines compound. category: pyrimidines

General procedure: To a solution of L-proline-melamine complex (3 mol%) in DMSO (2 mL) was added dimedone 0.025 mg (0.178 mmol), malononitrile (1 equiv) and benzaldehyde / isatin (1 equiv) and stirred at room temperature for 1-20 min. After completion of the reaction (monitored by TLC), ethyl acetate was added stirring and continued for another 5 min. The precipitate formed was filtered. Evaporation of solvent gave the crude product which was recrystallized using ethanol to give the pure compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,769-42-6, 1,3-Dimethylbarbituric acid, and friends who are interested can also refer to it.

Reference:
Article; Nagaraju, Sakkani; Paplal, Banoth; Sathish, Kota; Giri, Santanab; Kashinath, Dhurke; Tetrahedron Letters; vol. 58; 44; (2017); p. 4200 – 4204;,
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